P-CHLOROPHENOXYACETIC ACID METHYL ESTER

P-CHLOROPHENOXYACETIC ACID METHYL ESTER Property

Melting point:

35-37 °C(Solv: methanol (67-56-1))

Boiling point:

125 °C(Press: 10 Torr)

Density 

1.239±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to light yellow Solid

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P-CHLOROPHENOXYACETIC ACID METHYL ESTER Chemical Properties,Usage,Production

Synthesis

Anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1.5 eq.) was added batchwise to a N,N-dimethylformamide (DMF, 100 mL) solution of 4-chlorophenol (15 g, 116.67 mmol, 1 eq.) at room temperature. After stirring for 2 min, methyl 2-bromoacetate (13.3 mL, 140.01 mmol, 1.2 equiv) was added dropwise to the reaction system. Subsequently, the reaction mixture was heated to 80 °C and kept for 4 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, the unfolding agent was a hexane solution of 5% ethyl acetate), and after confirming the complete consumption of the raw materials, the reaction mixture was cooled to room temperature. The reaction solution was diluted with deionized water (100 mL) and extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, washed with saturated saline (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography (Combiflash, silica gel column), and the eluent was a hexane solution of 15% ethyl acetate. The eluate containing the target compound was collected and concentrated under reduced pressure to give methyl 2-(4-chlorophenoxy)acetate (22.5 g, 96.5% yield) as a light yellow liquid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.67 (s, 3H), 4.78 (s, 2H), 6.91-6.95 (m, 2H), 7.28-7.32 (m, 2H).

References

[1] Patent: WO2017/212423, 2017, A1. Location in patent: Page/Page column 71; 72
[2] Patent: WO2017/212425, 2017, A1. Location in patent: Page/Page column 68-69
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 3732 - 3735
[4] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12096 - 12099
[5] Chemistry - A European Journal, 2014, vol. 20, # 18, p. 5492 - 5500